Watch: Gloucester’s greasy pole contest remains summer’s craziest competition

Guts, glory, and grease were all present in abundance at the annual highlight of St. Peter's Fiesta on Cape Ann.

The worst thing you can do is tiptoe. No, if you want to walk (well, swim) away with the elusive flag in the annual greasy pole competition at St. Peter’s Fiesta in Gloucester, you’ve got to attack that 45-foot slimy protuberance in a full-on sprint.

Yes, for the majority of participants that will end in a quick slip and even quicker splash into the Atlantic Ocean off Pavilion Beach, sans flag. But for the few, the brave, the greasy-and-eventually-wet, it will result in glorious victory, and the hoisting onto shoulders and free drinks that follow.

The setup of the near-ancient Gloucester tradition — it started in 1931, and this was the 94th edition, having skipped a few years for COVID — is tough to explain: It’s a three-day contest that starts with a “courtesy round,” and ends with a grand finale on Sunday involving the previous day’s winner, past champions, and protégés. (Yes, there are protégés — greasy pole padawans, if you will.)

And this year, Derek Hopkins took home top honors for the sixth time, making him undefeated in his six pre- and post-COVID attempts. Not that his victory was foreordained: “I thought Stewy McGillivray was taking that thing down after his first walk,” Hopkins told the Gloucester Daily Times after his win, referencing an apparently actually real person. “But it was just very slippery out there today.”

Below, see video of Hopkins’ victory, along with shots of the good, the bad, and the greasy as they made their valiant attempts.